Playing Cupid
by SugarSkullDoll
Summary: When Cas asks about Valentine's Day, Sam can't help but nudge him and Dean together. Thanks to him, Dean and Cas go on a super fluffy date!


Playing Cupid.

"Sam, what is so important about Valentine's Day?" Castiel asked as they were grocery shopping a few days before the 14th. Sam looked over at Cas, who was staring at this huge gaudy display with pink and red and hearts everywhere. Sam grinned. He couldn't pass this up.

"It's a day to show your affection for someone you care for." Sam explained, watching as Cas's bright blue eyes looked up to him, before looking to the display again.

"Why?"

"It's just something humans do." He chuckled, watching as Cas's hands reach out for a pink bear holding an "I wuv U" heart.

"What would be appropriate to get then?" He looks at all of the different cards, candies and plush toys.

"Well...who would you get it for?" Sam smirks, already knowing the answer.

"Dean. And you, and Kevin." Cas nods, happy with his answer. Sam chuckles.

"Do you feel the same way about Dean as you do with me? Or Kevin?" Sam feels like he's talking to a child, but knows that Castiel isn't familiar with human traditions. Cas looks to him, calculating everything before he speaks.

"No. I...feel different about Dean then I do with you, and Kevin. You and Kevin are family. Don't get me wrong, Dean is too, but…" He raises his hand to his chest, thinking. "It hurts to be away from him, and when he smiles, I feel...content. Is that normal?" He looks alarmed to Sam, who has to bite his lip not to laugh out loud.

"It is when it comes to Dean. What do you want to get him then?" Cas smiled a bit, and they began to browse the Valentine's Day section.

It wasn't until the 13th that Dean realized something was up. Cas had been hiding away in his room, and wouldn't let Dean come in, no matter what. He kept saying he'd find out Friday, which after a while, Dean realized was Valentine's Day. He bolted downstairs to find his brother reading in the library.

"Sam! I've got a problem!" Dean rushed over to his younger brother. Sam rolled his eyes and put his book down.

"What's wrong Dean?"

"I think Cas is planning something for tomorrow!" Sam blinked, thinking before a slow smirk formed on his face.

"You mean-"

"Yes, Valentine's Day! How do I stop him?!"

"You want to stop him?" Sam tensed, and watched as Dean fought with himself internally. "Why? If he cares for you, let him show that."

"But it isn't the same…"

"The same as?"

"As...Dammit Sammy you know!" Sam never thought in all his years, he'd see Dean Winchester, his older brother and "Bad ass lady charmer" blush.

"As you feel for him?" Sam finished, and the blush got darker. This was too priceless. "Have you asked him?"

"What?! No!" Dean looked at Sam as if he told him he needed to behead babies for the next hunt.

"Why not?"

"Cause...he doesn't...I mean…"

"Why don't you find out tomorrow? Cas is a smart man...angel...you know." Sam wasn't use to saying Castiel was an angel again.

"But...shit what do I get him?!" Dean was now panicking, and looked over to Sam for help.

"Get him chocolates...or flowers...you know the normal stuff you get people on Valentine's Day?"

"He is anything but normal." Dean sighed, and an idea struck him. "I'll be back later, ok?" He grabbed his jacket from the other room and bolted to the garage. Sam smirked. This was too easy.

The next morning, after Dean had been up most of the night working on Castiel's present, he woke up smelling something wonderful. He groaned as he got up, looking at the mess he made trying to get everything ready, and sighed. He'd cleaned it up later. Grabbing a shirt and pulling it over his head, he opened the door to the hall only to find hearts and roses scattering the floor. It looked like they lead down to the kitchen, which Dean heard voices quietly talking, and the clanking of dishes. He walked down carefully, trying not to step in the path of cut out hearts and glitter. When he entered the kitchen, he was hit with the most amazing aroma he had been in contact with in years.

"Oh, good morning Dean." Castiel was at the stove, along with Sam, and smiled over at the hunter. Kevin was at the table, grinning away like a cat that had caught the canary, all while sipping his coffee.

"Morning." Dean's voice was raspy from sleep, and he cleared his throat. "What are you doing Cas?" He watched, noticing that Sam wasn't the one who was cooking. It was Cas.

"Making breakfast." Dean stopped, and paled a bit.

"Do you even know how to make breakfast Cas?"

"Of course not. Sam showed me how to make this." Sam looked back, and grinned at his brother in a knowing manner. "Get your coffee and sit down, it'll be done shortly." Cas motioned him towards the coffee that was already made. Dean grumbled, and saw a cup already made. He looked to Sam, who nodded to him that that was his. Dean grabbed it, walked over and sat next to Kevin. He took a sip, and stopped before he could ask Kevin whatever it was he was going to ask. The coffee was exactly like he liked it. He looked back up to the two making breakfast, and Sam was watching him. Dean raised an eyebrow and lifted the mug slightly, silently question his brother. Sam nodded towards Cas, meaning Castiel made his coffee. Dean could feel his face heat up, and went back to sipping it.

"So, what's the plan for today?" Dean asked, after a few minutes of silence. Sam finally left Cas to finished, and grabbed his own coffee, and sat down.

"Kevin and I were gonna do some research on the Tablets." Dean wrinkled his nose at the thought of research, and then realized Sam didn't mention him or Cas. He was about to question it, but was interrupted by Castiel putting a plate in front of him. Dean gulped, and looked down at the stack of chocolate chip pancakes, all with the right amount of butter and syrup on it that he'd like. What concerned him was that this was his favorite. He never really told anyone, only Sam knew, but he had a feeling that it wasn't Sam's doing that he got this. He looked to the other plates Castiel were putting down, and realized he was the only one with chocolate chip pancakes. He looked up to Cas, who was watching him, waiting for him to take a bite. He wasn't the only one, as Dean realized that Kevin and Sam were watching as well.

"What is with everyone?" Dean growled, glaring at his brother and the younger man at the table.

"We wanna see how you like the special pancakes." Kevin chuckled, grinning into his coffee cup. Dean was about to say something, but stopped and looked to Cas. He had the most hopeful look ever, waiting patiently to see if Dean liked them. Dean sighed, and cut himself a small piece off, before taking a bite. His eyes widened and he couldn't help but moan as he chewed. They were wonderful. He grinned as he tasted the melting chocolate along with the fluffy buttermilk pancakes, and with the butter and the syrup, was just...divine. He took another bite, and began to eat, grinning still. Castiel smiled, before going to clean up the mess he and Sam made.

"I take it those are good?" Sam chuckled.

"Good...Sammy you don't know the half of it! I haven't had pancakes like these since-" Dean stopped. The last time he had pancakes like this, he was 4. Before the fire, before the yellowed-eyed demon...his mother use to make him pancakes like this, on Sundays before everything went to hell, literally. Dean clears his throat, and finally finishes his sentence. "I haven't had these in a long time….Di-Did you make these by yourself Cas?" Castiel looked up from the sink, and smiled faintly at Dean.

"Yes Dean. I knew they were your favorite, so I made them. Sam helped me figure out the stove and helped me make sure I didn't burn them. Are they satisfactory?" Dean chuckles, finishing off the stack, before standing and going over to Castiel. The angel looked confused, and almost afraid like he was going to get punched for making Dean's favorite thing. Instead, he got pulled into a hug. Dean didn't care if Sam and Kevin were there; he just wanted to hug his angel, to show how much this meant to him.

"You bet your ass they were." He whispered to Cas, fighting back the tears in his eyes. Cas carefully hugged Dean back, and Dean could feel his smile as he nuzzled closer to the hunter. "Thank you Cas. They...they were perfect." He laughed, trying not to let it known he was crying. However, Castiel knew and after a pause, pulled away to look at Dean.

"Why are you crying then?" He spoke softly, and Dean realized that Sam and Kevin already left. He was relieved, cause he didn't want them to see this chick flick moment he was about to have with Castiel.

"Because they...reminded me of my mom. They were exactly what she uses to make me."

"I know."

"You...you know?"

"Dean, I'm the one who put your soul back together. I know what your favorite things are, even those you don't admit to. I know everything about you Dean." Castiel smiled. "Forgive me if I used that knowledge to my advantage. I...I wanted today to be special." Dean smiled back at Cas, chuckling.

"You did a good job at that. Is...this my valentine's day present?" Castiel blushed a bit, looking down.

"It's one of many, if...if you don't mind." Cas looked at him through his lashes, nervous suddenly. And adorable, in Dean's opinion.

"I don't. What else do you have planned?" Dean smirked, and loved the warm feeling that seemed to spread from his chest to the rest of him as he watched Cas smile.

"Well once I finish cleaning up the kitchen, I was wondering if you...wanted to go see a movie?"

"Wait, let me get this straight...you made me breakfast, and then you wanna go to a movie? Is...is this a date?" Dean asked, with a slight teasing tone. Castiel's face flushed, and he muttered something as he looked down, suddenly finding Dean's bare feet fascinating.

"It...it may be...if you...accept my offer of going to the movies?" Castiel's voice cracked at the end of his question, afraid that Dean would say no. Dean bit his lip, trying not to chuckle and give Cas the wrong impression as he tilted Cas's face back to look to him.

"I would love to Cas." Dean couldn't help but let his thumb brush the angel's lower lip, watching as it curled up to a smile. "Can I…" Before Dean could finish, Castiel leaned forward and gently kissed Dean. It was sweet and gentle and warm, and Dean wouldn't have it any other way. When Dean pulled back, Cas stared, again showing a bit of fear as if he did something wrong. "Do that?" he chuckled, and smiled as he saw the relief wash over Castiel's face.

"S-should we...get ready?"

"For the date?" Dean murmured, kissing Cas's cheek.

"Yes…" Cas sighed, and turned to meet Dean's lips for a second kiss. This one was more heated, Dean nibbling Castiel's lower lip, and when Cas gasped, he began to explore his angel's mouth. Castiel followed Dean's lead, exploring Dean's mouth as well. Finally Dean pulled away, gasping a bit. He loved seeing Cas like this, Hair all messy not only because he didn't brush it, but because Dean had his hands in it, his pupils blown with lust, and his lips swollen and shiny from their little make out session. Dean chuckled.

"Let's get ready Cas." He gave his angel a simple kiss, before helping him finish the dishes.

After the dishes were done and showers were taken (separately mind you) Dean met Castiel at the Impala. Dean noticed that Cas was wearing a nicer pair of black jeans and a tight black shirt with a red over shirt. He looked good, and Dean couldn't help but wonder if he cleaned up for the date. Even Castiel's normal messy hair looked like it finally got brushed and attempted to be styled. Dean grinned, and opened Cas's door for him.

"Ready?"

"Yes...I actually have a lot planned if...you don't mind." Castiel seemed bashful, which makes Dean smile more. After getting Cas settled and getting in himself, he listens to Castiel's instructions to get them to the theater. Dean couldn't help but start laughing, as he pulled up to the dollar theater that wasn't far from the bunker. Castiel looked confused, and slightly scared.

"I'm sorry...I don't mean to laugh, but...really? Do you know what this movie is about?" Dean pointed to the only movie playing at the moment. Castiel looked to the only showing of "My Bloody Valentine." and then looked back to Dean.

"No, but I thought it was a romantic movie, seeing as it's about Valentine's Day, right?"

"No Cas...It...it's not." Dean's laughing more now, before seeing the disappointment in Castiel's face in failing to find a 'Romantic' movie. He reaches out and pulls Castiel over by the back of the neck, and kisses him gently. "But it's perfect either way Cas. I just don't know if you'll like it. It's a horror movie." Cas thought about it, before nodding.

"It's nothing I haven't seen before hunting with you, I'm assuming?"

"No, you'll be fine then." Dean led them out of the impala, and headed towards the theater.

"That character Tom looked a lot like you Dean." Castiel told him as they left the theater, thinking about the movie they just watched.

"I don't think so Cas. But what'd you think about the twist?"

"You mean about Tom? Yes, I liked it. I wasn't expecting it." Castiel nodded to himself, before getting into their car.

"Alright, where to next Cas?" Dean was enjoying himself. For once, instead of trying to go out and get a one night stand, he was with someone he truly cared about, and was having a good time, all things considered.

"Well, I was thinking we could get lunch." He pointed out a shopping mall not that far from them.

"That sounds good, I'm starving. Wait, what about you?"

"its fine Dean...I knew you'd probably be hungry after the movie, so I figured we would go somewhere and get you something. Maybe take a...walk around the mall?" Castiel thought about this, as if he was trying to remember what he was told.

"Wait...did Sam tell you what to do on a date?" Dean asked, as he drove over to the mall that wasn't far from the theater.

"I...I wasn't sure what exactly to do with you today, if you had said yes…" Castiel blushed, embarrassed he was found out.

"It's fine Cas. Look, we'll grab something to eat like you said, and then look around if you want, ok? I don't mind. I...I'm happy as long as I'm spending time with you." Dean flushed as he admitted it, but looked over to the blue eyed angel.

"I am too Dean…" Cas admitted, and they both left to go to the mall. After eating at the food court, Dean and Cas walked around the mall, just talking. Simple, easy, and for some reason, fun to them both. As they moved past a crowd of teenagers, Dean grabbed Castiel's hand so he didn't lose him. Even after getting past the crowd, Dean kept holding Cas's hand. Castiel smiled, and gave it a gentle squeeze. Dean squeezed back, before pulling Cas into a store.

"Let's look around." Dean said, and let go of Castiel's hand so they could look. Cas nodded, and walked away from Dean. The shop they went to was a simple little 'hippy' store, as Dean would put it later, with all kinds of gems, dream catchers, and pendants. Castiel saw something that caught his eye, and smiled to himself. Best way to make Dean's present even better, was sitting right there in the display case. Dean himself was busy on the other side, looking at different gems and necklaces. Castiel quietly asked for the gift, and bought it without Dean even seeing. Luckily it looked like he was being bothered by the other sales rep on the other side, so it was easy to do. What he didn't realize, was that said sales rep was taking Dean's money for a present for Castiel.

"So, any plans for dinner?" Dean asked after they left the store, hands instantly going back to being held. Cas shook his head.

"I hadn't thought that far ahead…"

"Well, why don't we go home, I'll make burgers for everyone, then...if you want...you can come to my room and…" He paused, looking to Castiel. "We'll figure it out from there…?" He watched for any signs of him not wanting to, but relaxed when Cas smiled, and nodded.

"I'd like that."

When they got home, Dean rushed up to his room to clean up the mess he had made, and got his present ready for Cas. He'd give it to him tonight after dinner, and couldn't help but grin to himself at his cleverness. Afterwards, he went downstairs to start prepping burgers.

"So, how'd today go?" Dean looked over to his brother, who had a knowing grin on his face.

"It went fine. What'd you do today?" Dean didn't want to give out any details as far as their date.

"Research. While you two went out on your little date, Kevin and I did a ton of research." Sam teased. Dean flushed, and looked over to Sam. Before he could say anything, Sam patted his shoulder. "It's fine Dean. I knew this was coming, so don't hate me for wanting to help." Dean gave him a confused look. "Dude, think about it. Anytime we've come close to losing Cas, the way you act….come on, it's obvious. Only two who didn't seem to know were you and him. So, I nudged." Sam chuckled. Dean smiled, and nodded.

"Thanks Sammy." And he actually hugged his brother. Things had been rough after the fall of the angels, but still, his brother was there for him.

"Anytime." Sam then helped set the table, which soon found Kevin and Castiel, as Dean finished making burgers. He even made one for Castiel to try, knowing he didn't have to eat and could taste every molecule, but it was worth a shot. What surprised everyone was that Castiel actually ate the whole burger, and seemed to enjoy it. Dean flushed as the compliments he received not only from the angel, but the other two men sitting with them. After dinner, Dean got up to clean up, but Kevin stopped him.

"We got this dude. Go." He motioned to Cas, who blinked up at them as they were talking. Dean mumbled his thanks, and took Castiel's hand.

"Come on then...my room?" Dean smiled nervously.

"I will meet you there. I need to grab something from my room." Cas gave him a quick kiss before they separated. Inside his room, Dean began to pace. He was so nervous, he had no idea what he was going to do when Castiel actually showed up, he made sure his bed was made, and even brushed his teeth before Cas knocked on his door. Dean opened the door, and smiled at seeing Castiel, looking bashful as he entered.

"Hey Cas."

"Hello Dean." Dean closed the door, and when he looked back to his angel, he was surprised to see a nicely wrapped valentine's day present in front of him. Dean blinked, before taking it from Cas. "Happy Valentine's Day Dean." Dean chuckled, before going over to his bedside table, and handing Cas a pink bag with red and white paper sticking out.

"Happy Valentine's Day Cas." Castiel looked shocked at the fact that Dean got him something, before he took the bag from him, and sat on the bed. "Go ahead and open it." Dean spoke softly, wanting to see the look on his angel's face when he opened it. Castiel removed the paper, and pulled out a teddy bear. He smiled, but blinked a bit. He could smell chocolate, but when he looked into the bag, he didn't see any chocolate. He looked back at the bear, and then noticed the necklace. It was angel wings. Two, silver angel wings were dangling on a silver chain, and it was around the bears neck. He looked up to Dean, who smiled and nodded, before he went to pull the necklace off. It was then that he realized the bear smelled of chocolate. He paused, before placing his nose on top of the bears head and inhaled. It was pure milk chocolate. He smiled, and looked up to Dean.

"The bear…" He spoke softly.

"Well, I didn't think getting you chocolates would work...since…you know…" Dean scratched the back of his head, blushing. "Besides, I figured that would last longer. I got the necklace today though. I saw it and just...thought of you." Castiel put the necklace on, and smiled, holding the bear close.

"Thank you Dean...it means a lot to me." Dean smiled, happy to make his angel happy. He then looked to the package in his hand, and began to unwrap it. He smiled as he could feel the blue eyes of his...lover? Boyfriend? on him as he opened the small box. He held his breath as he stared down at his gift. He then looked up to Castiel, blinking as the tears formed.

"Is this-?"

"Yes. I kept it all this time. And, added something else." Castiel smiled, happy to see Dean so awestruck. Dean pulled out his necklace, the one that Sam had gotten him so many years ago, and saw that with the pendant, was a single black metal feather. It looked like it could've come from one of his wings, and it looked perfect next to his pendant. Carefully, he put the necklace on, and sighed, smiling at Castiel.

"It's perfect…" He whispered, before going to Cas, and capturing his lips. Cas moaned into his mouth as he allowed himself to be pushed down onto the bed. "Cas...I love you." He murmured as he kissed him again.

"I love you too Dean." Cas then pulled Dean closer, happy to have found out about this holiday in the first place.


End file.
